Hydrochloric Acid → HCID 118869917, compound

Participants

Reaction Conditions

Reaction Steps

7.0 g (20.0 mmol) of the 4-((4-amino-2-(octyloxy)phenyl)diazenyl)benzonitrile of Chemical Formula 1a-1 is dissolved in 200 mL of dimethyl acetamide (DMAc), 100 mL of acetic acid (AcOH), and 6.5 mL of 12 N HCl, and the resultant is maintained at 0° C. Subsequently, 1.4 g (20.3 mmol) of sodium nitrate (NaNO2) is dissolved in water, and the solution is slowly added to the reaction mixture dropwise. When the dropwise addition is complete, the reactant is maintained at 0° C. and agitated for one hour. Then, 2.9 g (20.3 mmol) of 1-naphthylamine is dissolved in methanol, the mixture is slowly dropwise added to the reaction mixture, and the mixture is agitated at 0° C. for one hour. Subsequently, the reactant is neutralized by using a sodium hydroxide (NaOH) aqueous solution to complete the reaction, and a solid precipitated therein is filtered. The mixture is purified through silica gel column chromatography (n-hexane:EtOAc=3:1), obtaining 7.9 g (15.7 mmol) of 4-((4-((4-aminonaphthalen-1-yl)diazenyl)-2-(octyloxy)phenyl)diazenyl)benzonitrile represented by the following Chemical Formula 1a-2. A yield is 79%.

Provenance & Evidence